(Cyclopropylmethyl)ammonium chloride → HCID 15925319, compound

HRID 704212Notes

Reaction equation

HRID 704212 reaction equation
Cl.[CH:2]1([CH2:5][NH2:6])[CH2:4][CH2:3]1.[CH3:7][N:8]([CH3:29])[CH2:9][CH:10]([N:12]1[C:25]2[CH:24]=[C:23]([C:26](=S)N)[CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:11].CC[O-:32].[Na+]>C(O)C.C(OCC)(=O)C>[CH:2]1([CH2:5][NH:6][C:26]([C:23]2[CH:22]=[CH:21][C:20]3[S:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH:10]([CH3:11])[CH2:9][N:8]([CH3:29])[CH3:7])[C:25]=3[CH:24]=2)=[O:32])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 2723922Sodium ethoxideHCID 15925238HCID 15925238, compound

Product 1

HCID 15925319HCID 15925319, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of cyclopropylmethylamine hydrochloride (5.4 g) dispersed in ethanol (25 cc) containing 10-[(2RS)-1-dimethylamino-2-propyl]-2-phenothiazinecarbothioamide (3.43 g) is added to a 0.05 M solution of sodium ethylate in ethanol (10 cc). The mixture is brought to 200° C. for 5 hours and then diluted with ethyl acetate (150 cc), washed with distilled water (2×100 cc), dried over magnesium sulphate and then concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. The residual solid is purified by chromatography on a column (height: 18 cm; diameter: 2.5 cm) of silica gel (0.6-0.02 mm), eluting with mixtures of ethyl acetate and cyclohexane in proportions (by volume) of 30:70 (2.5 liters) and 50:50 (1.1 liters), collecting 60-cc fractions. Fractions 50 to 59 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. to give N-cyclopropylmethyl-10-[(2RS)-1-dimethylamino-2-propyl]-2-phenothiazinecarboxamide (0.42 g), m.p. 90° C.

Workup

  1. washwashed with distilled water (2×100 cc)
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C
  4. customThe residual solid is purified by chromatography on a column (height: 18 cm; diameter: 2.5 cm) of silica gel (0.6-0.02 mm)
  5. washeluting with mixtures of ethyl acetate and cyclohexane in proportions (by volume) of 30:70 (2.5 liters) and 50:50 (1.1 liters)
  6. customcollecting 60-cc fractions
  7. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C.

Sources & evidence

ORD record
ord-4184ffbe7b64431faff44e31de17e535
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

Loading…